


Date Night With A DILF

by MyKinkIsPapyrus



Category: Undertale (Video Game)
Genre: Fluff, Fluff and Smut, Other, Papa Papyrus, Reader has no defined gender, Resurrected Skeleton Chara, SkeleChara AU (undertale), dilf, dilf Papyrus, ride that skeleton
Language: English
Status: Completed
Published: 2020-06-13
Updated: 2020-06-13
Packaged: 2021-03-03 23:46:39
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,317
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24693994
Author URL: https://archiveofourown.org/users/MyKinkIsPapyrus/pseuds/MyKinkIsPapyrus
Summary: A typical night spent with your lovely skeleton boyfriend and his child. Click for cuteness, thrills, and riding a Skeleton DILF.
Relationships: Papyrus (Undertale)/Reader, Papyrus (Undertale)/You
Comments: 4
Kudos: 42





	Date Night With A DILF

You couldn't wait to spend the evening with your new boyfriend and his child. Papyrus, as a skeleton monster, had the ability to raise the dead, and through a complicated process involving magic that you don't fully understand, that makes him the parent of whomever he brings back to life. Which is why even though he's only in his mid 20s, he has a child that is 11 years old. Mentally that is, physically they're closer to a hundred but a good chunk of that was spent in the dirt.

You knocked on the door and waited for someone to answer. Quickly, the door was flung open and a very tiny, very boney blur slammed into your legs with as much power as a 12 pound child skeleton could achieve.

"FOOLISH MORTAL! YOU HAVE RETURNED TO FACE YOUR APPROACHING DOOM!" They yelled, melodramatically, obviously joking. You picked up the little skeleton holding them up and away from you, like a powerful talisman that both awed and frightened you.

"Oh no! Whatever shall I do?" You began to (carefully) fall down, as if stricken with a spontaneous severe illness. You noticed at this point that Papyrus was approaching the door. You set Chara down before flopping onto your back, one hand dramatically thrown over your face. "If only there was someone tall, brave, strong, and ruggedly handsome to save me~"

Papyrus leaned on the door frame with his arms crossed and gave you a smug look. Chara meanwhile made choking sounds at the flirting going on around them and ran inside.

"ARE YOU ENJOYING THE WARM, DIRTY SIDEWALK, MY LOVELY HUMAN?" He snarked.

"I'm sorry to inform you I am dead and your child murdered me." You deadpanned.

"OH DEAR, HOW DID THEY DO THAT?"

"Weaponized cuteness."

"YES, THAT IS CHARAKTERNY'S TYPICAL MODUS OPERANDI." He held out a hand to help you up, easily lifting you to your feet in one movement. His strength amazed you every time he used it. "COME ON IN, I MADE DINNER, IT'S STROGANOFF, BUT WITHOUT THE MUSHROOMS BECAUSE CHARA HATES THOSE."

After dinner you watched The Nightmare Before Christmas, a movie which Chara adored. They cheerfully sang along to every song, and actually didn't gag in childish mock horror at the ending. Once it was over they decided the floor was their friend now, rolling across it to unleash pent up energy while singing This Is Halloween quietly.

It was getting close to bedtime for them but there was still some daylight to be enjoyed, so Papyrus used his blue magic to lift Chara into his arms while telling them they're going to work on their bullet patterns to burn off some of their pre-sleepytime energy. You followed them out and watched from the porch.

/\^/\^/\

"OKAY, NOW TRY TO IMAGINE THEM SPEEDING UP A LITTLE," Papyrus coached as a little bone ramp went from barely moving to steadily wobbling across the yard. You could tell by the adorable scrunched up look on Chara's face that they were working hard to keep the five or so attacks in formation as they slid along the ground.

"You're doing great, Chara! You've improved a lot since the last time I was here!" You called out in encouragement. Their face unscrunched slightly at the praise, the bones moving just a little bit faster. They completed the path they were meant to follow and were immediately dissipated.

Chara huffed from exertion, Papyrus kneeled by their side and told them how proud he was of their improvement, and you hopped off the deck to do the same.

"Your power grows every day, skelebaby." You said. Chara hissed, jokingly, at the cute nickname but you could tell they were still smiling.

"SOON I WILL BE ABLE TO CONQUER THE WORLD…" They spoke in an ominous tone, causing you and Papyrus to laugh.

"NO ENSLAVEMENT OF HUMANITY UNTIL YOU SHOWER, CHARA. SWEATY BONES AREN'T ALLOWED IN CLEAN SHEETS."

"I DON'T WANT TO, PAPA," They groaned in response but headed into the house to shower before bed anyways.

You stayed next to the porch for a little longer, Papyrus walking up to you and wrapping his arms around your waist. He leaned into you, his eye sockets closed as he rested his chin carefully on the top of your head and hummed. You both swayed from side to side, gently, as you watched the sun set.

"I'M GLAD YOU CAME OVER TODAY," He said into the top of your head, "I THINK CHARA REALLY LIKES YOU BEING HERE, TOO." You hummed.

"I'm glad about that, they really didn't like me at first." You replied. He laughed good-naturedly.

"THEY DON'T LIKE ANY HUMANS AT FIRST. THEY'RE NATURALLY WARY, BUT WARM UP IF THEY'RE TREATED WITH KINDNESS." You hum in response, softer this time, and snuggle further into his arms.

/\^/\^/\

You idly watched a movie as you waited for Papyrus to return. Every night he would read a full chapter of whatever book Chara was currently interested in to them before bed. About halfway through the movie he returned, climbing on top of you on the couch. He wrapped his arms around you and nuzzled his face into the crook of your neck.

"Hello there mister." You laughed, turning around in his arms to hold him in return. "What is it, Papy? You wanna snuggle?"

His arms tightened a little to give you a gentle squeeze while he began to nip at your neck, "SOMETHING LIKE THAT…" He pressed his pelvis against you as he slid one of his legs between yours. He nipped his way up your neck before pressing his teeth to your lips.

You parted your legs, one wrapping around him as you kissed and held each other. Both of your breathing was heavier as he rolled his hips against yours, one of your hands found his and you laced your fingers together, squeezing whenever the pressure of his pelvis would hit just right.

You leaned into his kiss before the movie caught your attention and reminded you that you were out in the open dry humping your boyfriend in his living room while his child likely wasn't even asleep. You pulled back and he stopped.

"WHAT IS IT, MY DEAR?" He sounded concerned and it warmed your heart.

"I think we should take this to your room." You smiled reassuringly at him. He promptly stood from the couch and swept you up into his arms before swiftly climbing the stairs.

In a moment you were on the plush mattress in his room, he had a racecar bed up until recently but retired it and bought a new bigger one now that you were coming over more often. A good time to break it in as any. He rapidly began to loosen the straps of his casual, every day, armor look, a quirk about him that you equally found attractive and fun to playfully tease him about. He set the metal chest piece off to one side before climbing over you, his teeth meeting your lips once more.

You reached down and squeezed his cock through his shorts, thumbing the head of it. Papyrus broke the kiss to breathe heavily into your shoulder; you took the opportunity to lean down and kiss and nip at his vertebrae. He nipped you in return before he began to pull your shirt off. Once you were both naked from the waist up you flipped him over so you were on top, grinding against his pelvis as you licked his neck bones again. Your hands found his and you interlaced your fingers as he let out choked moans.

"AH, JUST A LITTLE LOWER ON THE VERTEBRAE- OH, OH YES." He groaned low in the back of his nonexistent throat as he bucked his hips up into you reflexively. You managed to stay firmly planted on top of him and you rolled your hips down and along the bulge in his hot pants.

You pulled one hand from his grasp - still tenderly running your fingers over his metacarpals with the other - and began to undo his belt. With his newly freed hand he reached to the bedside table to pull out a bottle of lube. Unfortunately you had to part your other hand from his to pull his shorts off easier before being able to quickly rid yourself of your bottoms as well. You took a little bit of the lube and began to prep yourself while he stroked it onto his baculum. 

As relatively malleable the bones of his body tended to be on the surface, and despite how often you've had sex with him at this point, you both still liked to make sure there was plenty of lubrication to avoid awkward emergency room visits and eliminate the possibility of scarring situations for his child to stumble into.

Once you both felt sufficiently prepped and had wiped your hands off on a small towel, you positioned yourself over his cock, manually adjusting when needed as you slowly eased down onto him. He threw his head back and gripped the sheets tightly as his bones gently rattled. Once the head was all the way in you began to gingerly pump it in and out to ease it further into you. You reached down to grip his ribs.

He gasped sharply and grabbed onto your wrists, encouraging you to squeeze, and moving one of your hands to finger his sacrum from the interior of his pelvis. "Ah, f-fuck." He said, much more quiet than usual, likely in an attempt to prevent the whole street from hearing him.

Pressing a kiss to his teeth again as you finally managed to sink his entire cock into you, you used it as an opportunity to keep him from calling out as you set a viscous pace. His whole body tensed and trembled as you rode him at breakneck speeds, his moaning sufficiently muffled by you sliding your tongue into his mouth.

As he was sufficiently distracted you were the only one to hear the slightly muffled rattle of a door handle and squeak as it opened. You stopped instantly. Sans knew to teleport, that means Chara had left their room for some reason. Papyrus was still dazed until you looked him right in the eye sockets and said his child's name.

Instantly he had managed to pull the covers up from the bottom of the bed and up and over both of you, before rolling onto his side to make it look like you were both just cuddling, as well as summoning fast moving bones to drag all the discarded clothes that were still in the open under the bed. In all it took maybe 3 seconds or less, you weren't sure, time doesn't feel the same on that level of 'OH SHIT'.

You managed to calm your breathing enough to feign sleep as you heard the quiet shuffle of Chara's footie jammies on the hallway carpet, slowly passing the bedroom door. A few rogue creaks got you and Papyrus to relax slightly, knowing Chara was headed downstairs for a glass of water. Still, you both had to wait for them to return and go to bed, just in case, before you could resume your activities.

You decided, as you could distantly hear the running of water in the silent house, that this was torture. He was still in you, and while he seemed equally antsy he absolutely refused to move at all. After an eternity inside a minute you both finally heard the quiet creak of the stairs, the muffled shuffle of pajamas on carpet, and finally the distant click of a door shutting.

You counted the seconds in your mind and as soon as you hit 30, Papyrus rolled over to be on top of you, careful to keep the comforter draped over his back, before curling over you to kiss your neck and fuck you senseless all at once. You were glad that Papyrus' new bed was blessedly silent as he railed into you, otherwise his bedroom would sound like a construction site. He slid his arms between your back and the sheets, lifting you off them and pressing you into his ribs.

"You are so wonderful," he huffed into your ear, his fingers curling into your back slightly, "So wonderful~" he buried his skull into the crook of your neck, his thrusting more erratic. You clung to him, crossing your legs around his lower back, practically vibrating out of your skin from the stimulation as one of his hands moved to messily to drive you over the edge.

In seconds you came, biting gently into his collarbone to keep yourself from being too loud. Papyrus kept up the pace for a little longer, even as you clenched around him. Soon he also came, freezing in place save for the reflexive twitching of his pelvis trying to continue the movements despite being paralyzed by pleasure. You could feel his excess cum dripping out of you, vaguely through the haze of sex.

Almost blindly Papyrus felt around on the side table for a towel as he pulled out of you. He cleaned you off as you slowly came back to your senses, before folding the towel so no soiled side was outward facing and wiping himself off. He tossed the used towel over his shoulder - perfectly landing in the laundry basket - then collapsing onto you.

He rested his skull on your chest and gently squeezed his arms that were wrapped around you once more. He nuzzled you and hummed as you pulled the comforter up higher, your own arms falling to be draped on top of him. You idly stroked his back with one hand and the back of his skull with the other. It seemed that for once Papyrus had actually fallen asleep, which brought a smile to your face as you also drifted off.

**Author's Note:**

> Yeah it's me, I couldn't wait for someone else to make a fic dedicated to the DILF boy so I did it myself. If you know my main, that's cool but I like to keep them separate so don't mention it here. Been slowly chipping away at the 40 other projects I have. Hope to have some done soon. I'm still working on the kinktober prompt list from 2018, which will probably have pictures (okay inevitably have pictures because I would prefer drawing for some of the prompts VS writing them) and I'm hoping to bang out by July but man. Life is a fucking shitshow right now so I'm giving myself some slack in regards to personal, non-official deadlines.


End file.
